A utility player, Bailey was recruited to Melbourne from St Peters.
He kicked the winning goal in the Panasonic Cup final and was the only Melbourne player to appear in all 25 league games that they played, which included three finals.
[3] His 486 disposals for the season was second only to Greg Healy at the club and he also kicked 20 goals.
[3] In 1990 he made his way to Geelong, via the pre-season draft, but would only make one appearance for his new club.
[4] Bailey was a dual premiership player at Sandringham, in 1992 and 1994.